4'-Bromo-3-chloropropiophenone → 4-Bromo-alpha-(2-chloroethyl)benzenemethanol

HRID 45527Notes

Reaction equation

HRID 45527 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][CH2:10][Cl:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])[CH2:9][CH2:10][Cl:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 957904'-Bromo-3-chloropropiophenoneHCID 4311764Sodium borohydride

Product 1

HCID 108006384-Bromo-alpha-(2-chloroethyl)benzenemethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-Bromo-phenyl)-3-chloro-propan-1-one (1 g, 4.04 mmol) in tetrahydrofuran (9 ml) and water (0.58 ml) was added sodium borohydride (0.16 g, 4.28 mmol). The reaction mixture was stirred at room temperature for 2 hours, quenched with careful addition of water and extracted with ethyl acetate. The organic layers were separated, dried (MgSO4), filtered and concentrated to afford the title compound, which was used in the next step without further purification. LC/MS: (PS-A2) Rt 3.07 [M+H]+ No ionization.

Workup

  1. customquenched with careful addition of water
  2. extractionextracted with ethyl acetate
  3. customThe organic layers were separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-470292330b3f405fac111b7db227b355
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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